Triethylamine → HCID 67397491, compound

HRID 1037950Notes

Reaction equation

HRID 1037950 reaction equation
Cl.[NH2:2][C@@H:3]([C:5]1[S:9][C:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:7][CH:6]=1)[CH3:4].[F:17][C:18]([F:30])([F:29])[C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>CN(C)C=O>[F:30][C:18]([F:17])([F:29])[C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH:2][C@@H:3]([C:5]2[S:9][C:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[CH:7][CH:6]=2)[CH3:4])(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 67397013HCID 67397013, compound

Product 1

HCID 67397491HCID 67397491, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the vial containing (R)-tert-butyl 5-(1-aminoethyl)thiophene-2-carboxylate hydrochloride from Step 1 was added N,N-dimethylaminopyridine (3.91 mg, 0.0320 mmol), 4-(trifluoromethyl)benzenesulfonyl chloride (0.059 g, 0.24 mmol), N,N-dimethylformamide (2 mL), and triethylamine (0.178 mL, 1.28 mmol). The mixture was stirred at rt for 16 h and then evaporated. To the residue was added 1,2-dichloroethane (3 mL), sat. NaHCO3 solution (0.5 mL), and water (0.5 mL). After separation, the aqueous layer was extracted with 1,2-dichloroethane (2×3 mL). The combined organic phases were evaporated to dryness to give crude (R)-tert-butyl 5-(1-(4-(trifluoromethyl)phenylsulfonamido)ethyl)thiophene-2-carboxylate as a brown solid. LC-MS: (FA) ES− 434.

Workup

  1. customevaporated
  2. additionTo the residue was added 1,2-dichloroethane (3 mL), sat. NaHCO3 solution (0.5 mL), and water (0.5 mL)
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with 1,2-dichloroethane (2×3 mL)
  5. customThe combined organic phases were evaporated to dryness

Sources & evidence

ORD record
ord-2a85f760e26b48b389213b84bda85279
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

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